


It's high time, just one crack at life

by SinOfPride



Category: Supernatural
Genre: Crossdressing, Dirty Talk, Incest, Kink/Cliche Challenge, M/M, Manhandling, Mild Kink, PWP, Semi-Public Sex, Sibling Incest
Language: English
Status: Completed
Published: 2012-02-11
Updated: 2012-02-11
Packaged: 2017-10-30 23:28:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,518
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/337352
Author URL: https://archiveofourown.org/users/SinOfPride/pseuds/SinOfPride
Summary: <blockquote class="userstuff">
              <p>"I want it on record," Dean told the ceiling of the backstage dressing room, very carefully not looking at his brother or his own reflection in the mirror. "I think this is probably the worst plan you have <i>ever</i> come up with."</p>
            </blockquote>





	It's high time, just one crack at life

**Author's Note:**

> Title is from the song ‘Young Hearts Run Free’.

"I want it on record," Dean told the ceiling of the backstage dressing room, very carefully not looking at his brother or his own reflection in the mirror. "I think this is probably the worst plan you have _ever_ come up with." 

"Well, damnit Dean, what the hell else could we do?" Sam snapped back, adjusting the stuffing in his bra with a brisk movement of pure frustration. The damn thing kept sliding to a side. "We ran into a fucking haunted drag club, it's not like we had many choices here." 

"What about going in as _clients_ , Sam? We could pretend to like the scene! Why do we have to _be_ the scene?" Dean whined for what had to be a fifth time while his hand sneaked down to try and dislodge his panties from a particularly uncomfortable location. His skirt rode up when he adjusted it and Dean moaned out loud, carefully standing up from his seat on the ridiculously high heels he had on so he could straighten it all up. When he looked back up his gaze found Sam's in the mirror, and he felt his face heating up in yet another embarrassing blush that made Sam smirk at him. 

"Is it my fault the owner took one look and you and deemed you 'too pretty to waste on man's clothes' sweetheart?" Sam mocked him rudely, the effect promptly ruined when he reached for the lipstick on the dressing table he was leaning on and hastily painted some on himself. "Now get your pretty ass here and let me put make up on you. We have to walk out of here someday." 

"Do we really have to?" Dean asked sadly, looking down at his outfit. A red and black- rather painful, he might add- corset paired with a sinfully small miniskirt and high-heeled knee-high black boots. Not the mention the tiny red panties and the black garters he'd been forced to put on to complete the look. 

It wasn't fair, and he didn't understand why he'd been stuck with such a revealing _girly_ ensemble while Sam just got to wear a mid-thigh bright red dress with garters and flat shoes. While not exactly _manly_ , at least it covered more skin that Dean's clothes did. His short-ish blonde wig was waiting for him next to Sam's long brunette one, and he wasn't looking forward to make himself look even more like a girl with it and the make-up. 'Cause looking at himself in that mirror he was a total hot babe. A hot _female_ babe with a too broad back and muscled arms. 

"Stop pouting and come here," Sam barked at him and Dean sighed and complied, walking very carefully on his boots and trying to ignore Sam's mocking leer. Then Sam was on his face, painting his lips with shiny, fruity-smelling lip gloss and carefully lining his eyes in black, despite Dean's fidgeting attempts to make Sam ruin it. His wig came next, then Sam stepped back and Dean was left staring at the reflection of a wide-eyed girl with blushing cheeks, too-wide shoulders and actual hips, 'cause the corset was just that tight at the moment. Dean wasn't happy. "You look beautiful, you know," Sam whispered in his ear, making Dean roll his eyes. 

"Really funny," He snapped back, still trying to see himself in the reflection he was staring at. He was interrupted by Sam's huge hands grasping at his hips and pulling him back into Sam's cloth-covered erection, a move which made Dean look at Sam blankly. "Are you shitting me?" 

"I'd say not," Sam grinned at him, thrusting against him slightly. "Seriously, Dean, look at you. That corset has you so tightly bound you can barely move and that tiny little skirt keeps giving me glimpses of those red panties underneath. And your legs man, you should wear skirts more often. I'd have fucked you as soon as you laced up those boots you're teetering on."

"Shut the fuck up man, this is _not_ the time." Dean barked, too unhappy with the situation to take the words as anything other than further insult to his battered masculinity. “Let’s just get this over with.”

"Well, they are expecting us soon," Sam agreed seriously, still eyeing Dean's reflection in a way that was frankly making Dean nervous. Before he could say anything about it though, Sam's hand had sneaked beneath his miniskirt and had grabbed hold of his cock, stroking it to hardness with quick efficient pumps of his hand. The blood rushed away from Dean's head fast enough to force him to lean into Sam in order regain his balance. "Careful there Dean, you might just topple over."

"You smug fucker," Dean growled, deliberately rocking his hips back to earn a moan from Sam at the friction he created. "You're seriously gonna do this here?"

"Waste not and all that," Sam laughed breathlessly, biting Dean's earlobe and trailing a line of kisses down Dean's neck lightly enough to cause a shiver. 

"Bend over." Sam muttered and Dean shot a glare to him through the mirror, earning himself a sharp bite at the base of his throat that made him moan. "C'mon, there you go. I'd have you suck me off, but I'll ruin all that pretty make-up far too soon. We'll do it later, okay?" Dean just groaned an answer when Sam stroked him rhythmically in time with his words, carefully bending Dean over the dressing table as to prevent him from loosing his balance with the high-heels. Dean didn't meet his own eyes in the mirror as he adjusted his stance to fit Sam between his spread legs while Sam's other hand slowly slid up his skirt and pulled his red panties down to his thighs. 

"You're enjoying this far too much," Dean muttered crossly, biting his lip when Sam squeezed his sack in retaliation. The corset made his breath catch on his throat in the new pose, and Dean had to focus on his breathing to get used to the restriction. 

"Hush up," Sam told him, pulling back to admire the view and making Dean's face burn in humiliation. "Hey, none of that baby. You look gorgeous spread out like this, all mine." 

"Don't fucking call me that!" Dean bit out, choking on a moan when Sam took advantage of Dean's position and slapped at his exposed backside, making the skin tingle. "Sammy-"

"I said shut up, _baby_ ," Sam stressed mockingly, stealing a glance to the dressing-room's door that Dean caught in the mirror. "I'm pretty sure we didn't lock that and you don't want to be caught like this by all the drag queens, do you now?" Dean's eyes widened and Sam just laughed, efficiently pulling up his own red dress and freeing his cock from his own set of- slips! Dean was gonna _kill_ the fucker. "What? The panties were only for you Dean, they fit your pretty outfit to the tee." When Dean opened his mouth to answer, Sam squeezed his cock again, making Dean close his eyes and try to stifle his moan of pleasure. "Glad you agree. Now, let's see about some lube unless you wanna try it dry." 

Dean's eyes snapped back open and he glared at Sam, but it was wasted as his brother was eyeing their surroundings in search of a suitable lube substitute. When his eyes landed on a small jar of facial cream, Dean tried to grab for it, but Sam beat him to it and gleefully pulled it open, the scent of roses or lilies or some other girly flower shit filling the air around them. 

"C'mon!" Dean moaned miserably, but Sam already had the stuff on his fingers, and the next moan out of Dean's mouth had an altogether different ring to it when one of those long digits pushed into him without preamble. Dean was grateful for the wig that obscured his sight of the mirror in front of him whenever he lowered his head. He tried to push his hips back into the burn of Sam’s intruding finger, but with his legs caught in those boots he couldn't manage it, forced to just hold on for the ride while Sam muttered filth into his ear and teasingly thrust his hard cock against the small of Dean's back. 

The next finger was a tighter fit- it'd been a while since Sam had gotten all possessive like this- but Dean breathed through it, accidentally meeting Sam's heated eyes in the mirror and almost biting through his lip to stifle his moans as the hand on his cock stroked him relentlessly.

"Hey," Sam panted in his ear, licking a wet trail up Dean's exposed shoulder blades and kissing gently at his nape while his fingers eased Dean open with painful care. The hand on his erection disappeared for a second and then something smallish and cold was being slid between his lips. 

"Here Dean, suck on this. You're gonna slice your lip open like that." Sam explained softly but Dean had to look in the mirror to recognize his makeshift gag for what it was- a nail polish bottle that he clasped his lips around like a pacifier. The thought made his face burn again, but this time Sam just huffed a laugh against his neck. 

Dean moaned around the bottle on his tongue when those lips bit a mark into his right shoulder, while another finger slowly worked itself inside him, stretching him wide and a little painful at first, before the cream already in his entrance made the slide in easier. 

"Fucking gorgeous like this, Dean.” Sam moaned heatedly, but Dean didn’t look up until Sam twisted the fingers inside him none too gently. “So mine like this. Look at you, all flushed for me. I'm gonna fuck you now, okay? I can't wait any more. Gonna fuck you all bare back and then pull up your panties to cover the mess you'll have under your little skirt out there." 

Dean didn't even recognize the sound that came from his throat at that, but he was past the point of caring as Sam's fingers massaged over his prostate over and over again, driving him wild with need before pulling back and leaving him empty. He moaned piteously, muffled by the bottle in his mouth, but Sam was already hushing him, his erection circling Dean's hole like a promise before slowly sliding the head inside. Stretched uncomfortably full, Dean tried to move but again was unable to, sobbing out a breath that the corset made painful, while Sam told him to hold steady just like that, he was-

"Doing so good baby, right there," Sam muttered feverishly, almost slurring the words. "Gonna hold still for me? Don't wanna break your ankle, Dean." Yet he barely waited for the nod before he was thrusting all the way inside, making Dean's eyes roll back into his head. The hand holding his hip steady moved back to his neglected erection, making Dean whimper and tighten his muscles around Sam's cock. "So tight Dean, you're always so fucking tight. Perfect, just like that, you gonna come soon? Wanna come for me Dean?" 

Dean was way past the point of hearing the words, mind focused on the gradually fastening pace of Sam's thrusts inside him. The careful angle aimed at his prostate and made him see stars far quicker than he'd have liked, having him crying out in wordless pleasure while Sam patiently milked the orgasm from him. The hand around the head of his erection stroked him through the aftershocks gently, but Sam’s hips thrust hard into him just as Dean's world was slowly trying to come back into focus. Sam set a brutal pace that made Dean pant and try to sob out his breaths through his corset's restriction and the small bottle he was still sucking on to hold in his groans. 

"So good Dean, so fucking hot." Sam was groaning, incoherent with lust as he thrust harder and harder into Dean and made the table beneath them slam against the wall once, twice, three times in unmistakable rhythm. Then Sam froze suddenly and Dean felt the warmth of his release filling him, a string of curses and endearments hitting his ears as Sam leaned his forehead against Dean's sweaty back for long minutes of stillness. When it was over they were both still panting, harsh breaths filling the room until Dean couldn't hold back a squirm and a little moan while he spit out the nail polish from between his teeth. 

"Get off Sammy, your heavy ass is cutting my breathing off," He muttered, silently grateful when Sam carefully pulled out and helped him stand on his own two legs. He turned slowly and met Sam's hooded eyes with an uncertain grin, gasping when Sam's lips descended to thoroughly violate his mouth, huge paws holding his head still while Sam stole the breath from his lungs. When he finally pulled back, Dean barely had the mental capacity to mumble "So I take it you liked that?" breathlessly. 

Sam rested his forehead against Dean's as a slowly smile stole over his face, half-fond and half-wicked. Dean jumped when one of Sam's hands stole around his waist to gently finger his swollen entrance, making his legs wobble. As Dean leaned on Sam's chest for balance, that hand slowly pulled Dean's panties- damp with sweat- up his thighs to cover his backside again. Then he promptly patted Dean’s butt cheek lightly. 

"So," Sam said, promptly ignoring the death-glare Dean was sending in his direction and smiling way too smugly for a 6'4 guy in a tight, sparkly red dress. "Now that I’ve successfully marked my territory and made you look so well-fucked, we should go hunt some ghosts, huh?" 

"Marked your territory?" Dean repeated flatly, wiping the traces of lip-gloss from around his face and turning to face the mirror again to fix it. "Your ass is mine when we get back to the hotel, just for that." 

"Hey, I ain't complaining lady," Sam told him with all the innocence of a convicted man, deftly sidestepping the swat at his head Dean aimed at him. "Shall we, then?" 

"Just for the record," Dean informed him with a raised eyebrow while Sam walked ahead of him to the door, where the loud music- well, Madonna singing anyway- from the club beyond was the only explanation for why they hadn't had some 30 drag queens hollering at the free sex show. "You make one ugly-ass woman, Sammy."

"I'm just here to protect your virtue, lil' lady," Sam bowed mockingly, this time getting a high-heeled kick in the butt for his trouble. "Let's get this over with. I want to see if I can take those garnets off with my teeth."

"You propose to me with a diamond ring and I'm shooting you." Dean informed him calmly, slamming the door behind him and never once noticing the blinking red light of the security camera merrily recording in the dressing's room corner, by the mirror.


End file.
